NO174624B - Cyclopropylmalonanilate derivative for inhibition of plant growth, plant growth inhibiting preparation and use thereof - Google Patents

Description

The present invention relates to a cyclopropylmalonanilate derivative for inhibiting plant growth.

The invention also relates to a plant growth inhibiting preparation and the use of the aforementioned derivative as a plant growth inhibitor.

These and other features appear in the patent claims.

Certain malonic acid derivative compounds have been known in the prior art for some time, see e.g. US Patent Nos. 2,504,896 and 3,254,108. Some malonic acid derivative compounds are described in the prior art to give certain plant growth regulatory responses such as e.g. to prevent fruit drop, rooting of cuttings and formation of parthenogenetic fruit.

US Patent No. 3,072,473 describes N-arylmalonamic acids and their esters and salts, N,N'-diarylmalonamides, N-alkyl-N-arylmalonamic acids and their esters and salts, and N,N'-dialkyl-N,N'- diarylmalonamides which may be useful as plant growth regulators and as herbicides. Japanese Patent Publication No. 84 39,803 (1984) discloses malonic acid anilide derivative compounds which may be useful as plant growth regulators. The plant growth regulatory properties of substituted malonyl monoanilides are described by Shindo, N. and Kato, M., Meiji Daigaku Noogaku-bu Kenkyu Hokoku, Volume 63, Pages 41-58

(1984).

However, certain malonic acid derivative compounds and the use of malonic acid derivative compounds for inhibiting plant growth as described herein have not been previously described.

The present invention thus relates to a cyclopropylmalonanilate derivative for inhibiting plant growth, which is characterized by having the general formula:

where

Z'n are the same or different and are one or more selected from hydrogen, halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkoxy-phosphinyl, alkanoyl, aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkanoylamino, sulfonylamino, alkylsulfonylamino, alkanoyloxy, alkenyl or -CH=CHCH=CH-,

Y'6 is hydrogen or alkyl,

Y'7, Y'8, Y'9 and Y'10 are independently hydrogen, halogen or alkyl,

Y'41 is 0, S or NH,

R"10 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonium, an alkali metal or an alkaline earth metal or alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl , alkylsulfinylalkyl, alkanoylalkyl, aroylalkyl, dialkoxyphosphinylalkyl, diaryloxyphosphinylalkyl, hydroxyalkylthioalkyl, hydroxyalkyl sulfonylalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfonylalkyl, poly(oxyalkylene)alkyl, cyanoalkyl, nitroalkyl, alkylideneamino, carbamoylalkyl, alkylcarbamoylalkyl, dialkylcarbamoylalkyl, aminoalkyl, alkanoylaminoalkyl, alkanoyloxy -alkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl.

The invention also relates to a plant growth inhibiting preparation which is characterized in that it contains a cyclopropylmalonanilate derivative of formula 1.

Furthermore, the invention relates to the use of cyclopropyl malonanilate derivatives as plant growth inhibitors when applied to the plant in quantities from 0.0011 to 112 kg/ha, more particularly in quantities from 0.011 to 16.8 kg/ha and especially in quantities from 0.11 to 5.6 kg/ha.

Examples of cyclopropyl malonanilate derivatives in accordance with the invention which can be used to inhibit plant growth and which can be contained in the aforementioned plant growth inhibiting preparation are given in the following tables 1 and 2. The special compounds given in tables 1 and 2 above show a selection of the cyclopropylmalonanilate derivatives according to the invention and which can be used to inhibit plant growth.

The cyclopropylmalonanilate derivatives with the above-mentioned formula 1 and the intermediates used for their preparation can be prepared using methods known in the state of the art.

More particularly, the cyclopropylmalonanilate derivatives of formula 1 can be prepared according to the following general reaction principle:

wherein Z'u, Y'7, Y'8, <Y>'9, Y'10, Y'41 and R"10 are as indicated above and Y'21 is NH or N(alkyl).

Reactions of this general type for the production of malonic acid derivative compounds and process conditions are described by e.g. Richter, G.H. "Textbook of Organic Chemistry", 3rd ed., John Wiley and Sons, NY, p. 486, according to the known Schotten-Baumann procedure.

Specific and particularly preferred cyclopropyl malonanilate derivatives in accordance with the invention are selected from among the following compounds: US patent application D-152 98 filed on the same date as the present application describes synergistic plant growth regulatory compositions containing (i) an agent that induces an ethylene response or an ethylene-type response and (ii) a cyclopropylmalonanilate derivative of formula 1. This application is incorporated herein by reference. The above-mentioned US patent application D-15298 corresponds to the international application with publication no. WO-A-87/05781.

The cyclopropylmalonanilate derivatives of formula 1 have been found to significantly inhibit plant growth compared to untreated plants under similar conditions. In addition, the said derivatives according to the invention are mainly non-phytotoxic to growing plants.

As used herein, an effective amount of a cyclopropylmalonanilate derivative for inhibiting plant growth refers to a growth inhibitory effective amount of the compound sufficient to inhibit plant growth. The effective amount of the compound may vary within wide limits depending on the particular compound used, the particular plant being treated, environmental and climatic conditions and the like. The amount of compound used preferably does not cause significant phytotoxicity, e.g. leaf burn, chlorosis or necrosis of the plant. In general, the compound can preferably be applied to plants in a concentration from 0.011 to 16.8 kg/ha as described in more detail below.

The cyclopropyl malonanilate derivatives included in formula 1 can be used in accordance with a number of different conventional methods known to the person skilled in the art. Mixtures containing the compounds as active ingredient will usually comprise a carrier and/or diluent which is either in liquid or solid form.

Suitable liquid diluents or carriers include water, petroleum distillates or other liquid carriers with or without surfactants. Liquid concentrates can be prepared by dissolving one of these compounds with a non-phytotoxic solvent such as acetone, xylene, nitrobenzene, cyclohexanone or dimethylformamide and dispersing the active ingredients in water using suitable surface-active emulsifying and dispersing agents.

The choice of dispersing and emulsifying agents and the amount used is governed by the nature of the mixture and by the agent's ability to facilitate the dispersion of the active ingredient. In general, it is desirable to use as little of the agent as possible in accordance with the desired dispersion of the active ingredient in the spray so that rain does not re-emulsify the active ingredient after it has been applied to the plant and wash it off the plant. Non-ionic, anionic and cationic dispersing and emulsifying agents can be used as e.g. the condensation products of alkylene oxides with phenol and organic acids, alkylaryl sulphonates, complex ether alcohols, quaternary ammonium compounds and the like.

When producing wettable powder mixtures or dust mixtures, the active ingredient is dispersed in and on a suitably divided solid carrier such as e.g. clay, talc, bentonite, diatomaceous earth, bleaching earth and the like. When designing the wettable powders, the above-mentioned dispersants as well as lignosulfonates can be included.

The required amount of active ingredient can be applied per targets treated in an amount of from 0.935 1 to 187 1 or more of liquid carrier and/or diluent or in an amount of from 560 g to 56 kg of inert solid carrier and/or diluent. The concentration in the liquid concentrate will usually vary from 5 to 95% by weight and in solid mixtures from 0.5 to 90% by weight. Satisfactory sprays or dusts for general use contain from 0.0011 to 112 kg of active ingredient per ha, preferably from 0.011 to 16.8 kg of active ingredient per ha, and in particular from 0.11 to 5.6 kg of active ingredient per ha.

Mixtures that can be used according to the invention can also contain other possible components such as e.g. stabilizers or other biologically active compounds as long as they do not weaken or reduce the activity of the active ingredient and do not damage the plant being treated. Other biologically active compounds include e.g. one or more insecticides, herbicides, fungicides, pneumatides, miticides, plant growth regulators or other known compounds. Such combinations can be used for known or other purposes with each component and can provide a synergistic effect.

The cyclopropylmalonanilate derivative compounds of general formula 1 are preferably applied to the plants under substantially average or normal growth conditions. The derivative compounds according to the invention can be applied during the plant's vegetative growth phase or the plant's reproductive growth phase to achieve plant growth inhibition. Such compounds are useful in agriculture, horticulture and related fields and can generally be applied to both gymnosperms and angiosperms, particularly to vegetation such as woody plants and turf to inhibit plant growth. The connections are e.g. useful for regulating the height of vegetation in road areas and for inhibiting growth after pruning trees and bushes etc. without any harmful ecological effect.

As used herein, the term plants generally refers to any agricultural or horticultural plants, woody plants, ornamental plants, and turf. Woody plants that can be treated with the derivative compounds of formula 1 include e.g. red maple, mulberry fig tree, red oak, American elm, lime tree, ginkgo, oak tree, ash, maple, apple tree, Chinese elm, wild alder, Russian olive tree, silver elm, sugar elm, water oak, poplar, pine tree, etc. Other plants that can be treated with the compounds of formula 1 according to the invention include e.g. corn, cotton, sweet potatoes, white potatoes, alfalfa, wheat, rye, rice, barley, oats, sorghum, dry beans, soybeans, sugar beets, sunflowers, tobacco, tomatoes, canola, hardwoods, citrus fruits, tea, coffee, olives, pineapple, cocoa, banana, sugar cane, oil palm, garden bed plants, woody shrubs, turf, ornamental plants, evergreens, trees, flowers and the like.

The derivative compounds according to the invention are effective in inhibiting plant growth. The compounds have a high margin of safety in that when used in sufficient quantity to produce a growth inhibitory effect, they will not burn or damage the plant, and they resist weathering which includes awash by rain, decomposition by ultraviolet light, oxidation or hydrolysis in the presence of moisture, or at least such cleavage, oxidation and hydrolysis which will particularly reduce the desired plant growth inhibiting property of the active ingredient or give undesirable properties such as e.g. phytotoxicity of the active ingredients. Mixtures of the active compounds can be used if desired, as well as combinations of active compounds with other biologically active compounds or components as stated above.

The invention will now be illustrated using the following examples.

EXAMPLE I

Preparation of ethyl 1-(2-methyl-4,5-dichlorophenylamino-carbonyl)cyclopropanecarboxylate

5.53 g (0.03 mol) of 2-methyl-4,5-dichloroaniline, 3.18 g (0.03 mol) of triethylamine and 190 ml of tetrahydrofuran solvent are introduced into a nitrogen-flushed round bottom flask. Under vigorous stirring, 5.55 g (0.03 mol) of ethyl 1-chlorocarbonylcyclopropane carboxylate prepared in Example V was added in one portion after which the mixture was stirred at ordinary temperature for 6 hours. A precipitate of triethylamine hydrochloride was then filtered off and the filtrate was evaporated in vacuo to give a pale yellow solid. The solid was taken up in ether and the solution was washed with water, dried over magnesium sulfate and the solvent was evaporated to give a yellow powder. Recrystallization from ethyl acetate hexane gave 4.51 g (0.01 mol) of ethyl 1-(2-methyl-4 ,5-dichlorophenylaminocarbonyl)cyclopropane carboxylate with m.p. 105-107°C. Elemental analysis of the product indicated the following:

Analysis: C14H15C12N03

Calculated: C, 53.18; H, 4.78; N, 4.43

Found: C, 53.41; H, 4.76; N, 4.44

This compound is hereinafter referred to as compound 77.

EXAMPLE II

In a similar manner to Example I, other compounds were prepared. The structures and analytical data of compounds 78 to 96 are given in Table A below.

EXAMPLE III

Preparation of 1-(2-methyl-4,5-dichlorophenylamino-carbonyl)cyclopropanecarboxylic acid

A solution containing 0.34 g (0.006 mol) of potassium hydroxide and 0.109 g (0.006 mol) of water in 80 ml of ethanol was prepared in a 250 ml round bottom flask. With cooling to a temperature of 0°C in an ice/NaCl bath and stirring, a solution of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate prepared in Example I in a small volume of ethanol was added and the mixture was warmed to room temperature with stirring over a 72 hour period. The mixture was evaporated in vacuo to give a white solid residue which was dissolved in water and extracted twice with ether. The ether extracts were removed. The aqueous solution was acidified to pH 2 with a 25% HCl solution causing separation of a solid which was taken up in ether, and the acidified aqueous phase was extracted four times. The combined ether extracts were dried over magnesium sulfate and evaporated in vacuo to give a white solid. This white solid was washed with water and dried in a vacuum oven to give 1.85 g (0.006 mol) of 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylic 1 acid of m.p. 248-251°C.

Elemental analysis of the product indicated the following:

Analysis:<c>12<H>ii<C>12N03

Calculated: c, 50.02; H, 3.85; N, 4.86

Found: C, 50.51; H, 4.31; N, 4.83

This compound is hereinafter referred to as compound 110.

EXAMPLE IV

In a similar manner to Example III, other compounds were prepared. The structures and analytical data of compounds 111 to 1<*>28 are given in the following Table B.

EXAMPLE V

Preparation of ethyl-1-chlorocarbonyl cyclopropane carboxylate

Into a stirred solution containing 15.1 g (0.27 mol) of potassium hydroxide in 240 ml of ethanol and 4.83 g (0.27 mol) of water was added dropwise and while cooling at a temperature of 0°C, 5.0 g (0.27 mol) diethyl 1,1-cyclopropane dicarboxylate. The mixture was stirred for about 16 hours at room temperature. The solvent was removed under reduced pressure to give a white residue which was dissolved in water and extracted with ether. The aqueous solution was acidified to pH 2 with 25% aqueous hydrochloric acid and the organic acid was extracted from the aqueous suspension with ethyl ether (4 x 400 mL). The ether extract was dried over magnesium sulfate and evaporated in vacuo to give the monocarboxylic acid as a clear liquid. The clear liquid was dissolved in 300 ml of methylene chloride, after which 74 g (0.62 mol) of thionyl chloride was added, and the resulting mixture was then heated under reflux for about 16 hours. Volatiles were removed under reduced pressure to give 45.7 g (0.25 mol) of ethyl 1-chlorocarbonyl cyclopropane carboxylate. NMR analysis of the product indicated the following: NMR (COCl3): δ 1.22-1.50 (t, 3H), 1.75

(s, 4H), 4.1-4.52 (q, 2H) resp.

This compound is hereinafter referred to as compound 155.

EXAMPLE VI

Effect of representative cyclopropylmalonanilate derivatives on plant growth inhibition - field beans and wheat

Solutions of the test compounds listed in Table C below were prepared by dissolving 68.8 mg of the particular compound in 5.5 mL of acetone and then adding water to a final volume of 11.0 mL. If the liquid became cloudy when the water was added, the use of water was stopped and acetone was added to a final volume of 1.0 ml. The obtained output resolutions contained 6255 parts per million, expressed by weight, of the particular compound. The test concentration in parts of the test compound per parts per million by weight of final solution used in the growth inhibition tests in Table C were obtained by appropriate dilutions of the starting suspension with acetone and water (50/50 v/v).

Seeds of broad beans, wheat, velvetleaf, snake cucumber, sun sedge, flax, buckwheat, tomato, perennial rye, marigold, soybean, chickpea, millet and peas were planted in sandy loam soil in a planter with the following dimensions: 8.99 cm width x 20.1 cm length x 2.54 cm height. Twelve to fourteen days after planting at the time when the first trifoliate leaf of the cut bean is 3.0 cm in length, each concentration of the test compounds shown in Table C was applied to a planter as a foliar spray using a pressure sprayer set at an air pressure of 78.9 • 10<3>Pa (all boxes were sprayed with an amount of active ingredient of 4.48 kg/ha). As a control, a water-acetone solution containing no test compound was also sprayed onto a planter. When dry, all the plant boxes were placed in a greenhouse at a temperature of 2 6.7°C ± 2.8°C and a humidity of 50% ± 5%. Visual indications of growth inhibitory activity were observed and noted 10 to 14 days after treatment.

Visual observations of growth inhibition were noted using a numerical grading system. Numerical grades from "0" to "10" were used to denote the degree of growth inhibitory activity observed compared to the untreated control. A rating of "0" indicates no apparent response, a rating of "5" indicates 50% more growth inhibition compared to the control and a rating of "10" indicates 100% more growth inhibition compared to the control. Stated in a similar manner, a rating of "5" indicates that the increase in plant growth is only half as great as the control or that the plant has increased its growth at a rate half that of the control. This grading system indicates inhibition of plant height compared to the untreated control. The results are shown in the following table C.

The results in table C show that treatment of plants with cyclopropylmalonanilate derivatives causes significant growth inhibition compared to untreated control plants.

EXAMPLE VII

Effect of representative cvclopropylmalonanilate derivatives on inhibition of plant growth - wheat

Solutions of the test compounds listed in Table D below were prepared by dissolving the compounds in acetone/water (50:50 vol/vol) containing 0.05 vol% Triton X- . 100 surfactant which is commercially available from Rohm and Haas Company, Philadelphia, Pennsylvania. As detailed below, these solutions of test compounds were applied to wheat at a concentration of 0.56 kg of active ingredient per ha or 1.12 kg of active ingredient per have. Wheat seeds were planted in sandy clay soil in a planter with the following dimensions 8.89 cm width x 20.1 cm length x 2.54 cm height. Eight days after the appearance of wheat's 2-3 leaf growth stage, each concentration of the test compounds listed in Table D was applied to a planter box as a foliar spray using a pressure sprayer set to an air pressure of 78.9 • 10<3>Pa (all planters were sprayed with a volume corresponding to 1122 1 per ha). As a control, a water-acetone solution without test compound was also sprayed onto a planter. After drying, all the plant boxes with wheat were placed in a greenhouse at a temperature of 2 6.7 ± 2.4°C and a humidity of 50% ± 5%. Visual indications of growth inhibitory activity were observed and noted 14 days after treatment. Visual observations of growth inhibition were noted using a system of percentage grading. These percentage gradations from 0 to 100 were used to denote the degree of growth inhibitory activity observed compared to the untreated control. A 0% rating indicates no visible response, a 50% rating indicates that the increase in wheat growth is only half that of the control or that the wheat has increased its growth at a rate half that of the control, and a 100% rating indicates a maximum response. This scoring system indicates any inhibition of wheat height compared to the untreated control. The results are shown in the following table D. The results in table D show that treatment of wheat with cyclopropylmalonanilate derivative compounds gives significant growth inhibition compared to untreated control wheat.

EXAMPLE VIII

Effect of representative cvclopropylmalonanilate derivatives on inhibition of plant growth - red maple and sycamore maple

Solutions of the test compounds shown in the following Table E were prepared by dissolving the compounds in acetone/water (50:50 vol/vol) containing 0.1 vol% Triton X-100 surfactant commercially available from the Rohm and Haas Company, Philadelphia, Pennsylvania. As detailed below, these solutions of test compounds were applied to red maple and sycamore maple in a concentration of 1.12, 2.24 or 4.48 kg of active ingredient per have.

Bare seedlings of red maple (Acer rubrum) and plane maple

(Platanus occidentalis) was obtained commercially and grown in 3.8 liter plastic containers containing a sandy loam soil. The seedlings were kept in a greenhouse at a temperature of 26.7 ± 2.7°C and a humidity of 50% ± 5%. After a period of 1 month, the shoots were removed from the growing trees except for a dominant main shoot with a length of 10.16-15.24 cm. At this time, each concentration of the test compounds shown in Table E was applied to separate trees as a foliar spray using a pressure sprayer set at an air pressure of 78.9 • 10<3>Pa (all trees were sprayed with a volume equivalent to 1122 l/ have). As a control, a water/acetone solution containing no test compounds was also sprayed on certain trees. After drying, all trees were returned to the greenhouse for a period of 1 month. Measured indications of growth inhibitory activity were observed and noted at this time (1 month after treatment).

Percent inhibition of shoot elongation as indicated in Table E was determined by actual measurement of the shoot on each tree and compared to the untreated control. The average shoot length of the untreated control trees was 48 cm for red maple and 53 cm for plane maple. The results in Table E represent the average of three repetitions.

The results in Table E show that treatment of red maple and sycamore maple with certain cyclopropyl malonanilate derivative compounds causes significant growth inhibition compared to untreated control trees of red maple and sycamore maple.

EXAMPLE IX

Effect of representative cyclopropylmalonanilate derivatives on inhibition of plant growth - red maple and sycamore maple

Solutions of the test compounds listed in Table F below were prepared by dissolving the compounds in acetone/water (50:50 v/v) containing 0.1% by volume Triton X-100 surfactant commercially available from the Rohm and Haas Company, Philadelphia, Pennsylvania. As detailed below, these solutions of test compounds were applied to red maple and sycamore maple in a concentration of 1.12 or 2.24 kg of active ingredient per have.

Bare seedlings of red maple (Acer rubrum) and sycamore maple (Platanus occidentalis) were obtained commercially and grown in 3.8 liter plastic containers containing a sandy loam soil. The seedlings were kept in a greenhouse at a temperature of 26.7 2.7°C and a humidity of 50% ± 5%. After a period of 3 months, the growing trees were pruned to a 50% reduction in height. 24 days after pruning, each concentration of the test compounds listed in Table F was applied to separate trees as a foliar spray using a pressure sprayer set to an air pressure of 78.9 • 10<3>Pa (all trees were sprayed with a volume equivalent to 1122 1 per .ha). As a control, a water-acetone solution without test compound was also sprayed on certain trees. After drying, all trees were returned to the greenhouse for a period of 45 days. Visual indications of growth inhibitory activity were observed and noted at this time (45 days after treatment).

Percent inhibition of regrowth as indicated in Table F was determined by visual observation of the regrowth of each tree compared to the untreated control. A 0% rating indicates no visible response, a 50% rating indicates that the increase in growth is only half that of the control or that the tree has increased in growth at a rate half that of the control, and a 100% rating indicates a maximum response. This grading system indicates any inhibition of regrowth compared to the untreated control. The results in Table F correspond to the average of three repetitions.

The results in Table F show that treatment of red maple and sycamore with certain cyclopropylmalonanilate derivative compounds leads to significant inhibition of regrowth compared to untreated control trees of red maple and sycamore.

Claims (7)

1. Cyclopropylmalonanilate derivative for inhibiting plant growth, characterized in that it has the general formula: where Z'lx are the same or different and are one or more selected from hydrogen, halogen, haloalkyl, polyhaloalkyl, polyhaloalkoxy, alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, aryl, aryloxy, arylthio, arylsulfonyl, nitro, cyano, dialkylphosphinyl, alkanoyl , aroyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkanoylamino, sulfonylamino, alkylsulfonylamino, alkanoyloxy, alkenyl or -CH=CHCH=CH-, Y'6 is hydrogen or alkyl, Y'7, Y'8, Y'9 and Y'10 are independently hydrogen, halogen or alkyl, Y'41 is 0, S or NH, R"10 is hydrogen, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl)ammonium, an alkali metal or an alkaline earth metal or alkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, mercaptoalkyl, alkylthioalkyl, arylthioalkyl, aryloxyalkyl, alkylsulfonylalkyl . -alkyl, alkoxycarbonylaminoalkyl, cyanoaminoalkyl, carbamoyloxyalkyl, alkylcarbamoyloxyalkyl, dialkylcarbamoyloxyalkyl, alkoxycarbonyloxyalkyl, alkoxycarbonylthioalkyl, aminosulfonylalkyl, alkylaminosulfonylalkyl or dialkylaminosulfonylalkyl. 2. Cyclopropylmalonanilate derivative as stated in claim 1, characterized in that the derivative is a compound selected from among the following: 3. Cyclopropylmalonanilate derivative as stated in claim 1 or 2, characterized in that the derivative is in the form of a salt. 4. Cyclopropylmalonanilate derivative as stated in claim 3, characterized in that it exists as an alkali metal, alkaline earth metal, ammonium, alkylammonium, polyalkylammonium, hydroxyalkylammonium, poly(hydroxyalkyl) ammonium salt or mixtures thereof. 5. Plant weight inhibiting preparation, characterized in that it contains a cyclopropylmalonanilate derivative as specified in claim 1. 6. Use of cyclopropylmalonanilate derivatives as specified in claims 1-4, as a plant growth inhibitor when applied to the plant in amounts from 0.0011 to 112 kg/ha. 7. Use as stated in claim 6 in quantities from 0.011 to 16.8 kg/ha, in particular from 0.11 to 5.6 kg/ha.